On The Streets of Palo Alto
by deandeanthemurdermachine
Summary: Sam, Dean, and Cas begin to explore their newfound relationship on the streets of Palo Alto as the clock counts down to the New Year. To celebrate they, of course, all lose their virginity. Because what's New Years without a sloppy threesome? (written for jocstiel and songsaboutsleep's ficlet exchange on tumblr.)


Rosworms' Wincestiel Fic

On The Streets Of Palo Alto

Sam, Dean, and Cas begin to explore their newfound relationship on the streets of Palo Alto as the clock counts down to the New Year. To celebrate they, of course, all lose their virginity. Because what's New Years without a sloppy threesome?

It was a dating site that started it all.

They'd all known each other, however vaguely, before they'd really met. They were all students in California, and they were all a litle bit gay.

Honestly, Gabriel had talked him into it. Gabe was always spouting off about how he needed to get out more, go and "see what's out there" as he put it.

But Castiel wasn't interested. No, he was happy to go on and stay a quiet Visual Arts major in the B dorms, with a pothead for a roommate and a lonely ashtray on the windowsill.

And then Gabe had to go and interfere. The first thing Gabe does with his email address ("we've got to stay in touch somehow, right?") is sign him up for a dating site.

But not any normal dating site. Oh, that just wouldn't be Gabriel.

The name of the site was We3. It was a site for polygamous couples. And on his first day, he got an offer from two men.

If this didn't work out, he was going to kill Gabriel.

He checked over their profiles first chance he got. It was New Years Eve, after all, and why shouldn't he have a date? Or two?

The first one was for a student in Stanford. His name was Sam Campbell, and even he couldn't deny that he was _very _aesthetically pleasing to look at. He was pan, and was looking for people in his area.

The second one, also, was for a student in Stanford. His name was Dean Winchester, and he too was quite the sight for sore eyes. He was bi, and looking for two faithful companions. He snorted as he read that last part. It sounded like something out of a PetSmart commercial.

He said yes to both. It was New Years Eve. Why the fuck not?

In his messages, he agreed to meet with both of them at the corner of Main and Twenty-First at six o'clock that night to go to the big city-wide New Years Party. They both quickly zipped back their replies, with a "hell yes" from Dean, and a "sure, why not" from Sam.

And it was five-forty five, and he still didn't have a damn thing to wear.

He perused his closet yet once more, only to find nothing that would really work. Most everything he owned was splattered in some kind of paint, or smudged with charcoal, or dotted with ink. What the hell was he supposed to wear?

Then he spotted it. At the very back of the closet, behind the red-splattered jeans (he'd had to explain to Gabriel, repeatedly, that no, it wasn't blood, and why do you keep trying not to laugh?) and the screen-printed shirt of Man With Apple by Salvador Dali (Gabriel sure had taken a shining to that one over Winter Break) was a pristine, white dress shirt. Thank God.

Maybe if he rolled it up at the sleeves, it'd look a bit better.

With some more digging, and yet more ruined clothing, he managed to find a pair of black jeans and a pair of oxfords that weren't completely disgusting. He slapped on his tie and adjusted the dusty crème beanie that he always wore on his messy, black hair. He genty out his glasses onto his face (they were a bit crooked, what did you expect when your niece grabbed them off of your face and began to wave them around? And, of course, Gabriel had laughed it off.) He shoved his wallet in his back pocket and began to leave his dorm room. His tattoo sleeves shone in the pale streetlight coming in from the window as he left.

It was 5:51 pm.

He walked briskly, as to not lose any time. He was already behind, why should he keep the poor gents waiting?

Then, he froze. _He hadn't told __**either**__ of them that there was going to be someone else there for the same purpose._

He whipped out his phone, the pale light of the streetlamps glinting of the dark screen. It was dead. _Figures._

He kept walking faster, hoping to intercept at least one of them before the other one got there. This was going to get really awkward, very quickly, if he at least didn't explain the situtation to one of them.

He was three blocks away.

His tan oxfords beat against the pavement as he increased his pace. The cold air whoosed around him, and he was beginning to wish that he'd brought a jacket.

Two blocks.

He could see them under the lamps now.

One block.

And they looked even better in person.

Zero blocks.

"So, I hope you guys know each other." He said.

Sam and Dean turned to face him. "Oh, don't worry." Dean said. "Our dorms are right next to each other. We figured it out pretty quick."

Castiel's face blushed bright red. Well, this hadn't been the way he intended it to go down, but he wasn't going to give up now.

"Do you guys, uh, wanna go grab a meal before the fireworks start?" he asked.

They nodded, and began in the direction of the Crossroads Inn and Diner.

The Crossroads had the best food in all of the county, everyone knew that. His only hope was that he could manage to get them all a table. It got pretty packed on most nights, but on holidays it was like a freeway at rush hour.

Dean nudged up against him. "Don't worry, I called ahead. Crowley's got a table waiting for us."

He sighed in relief. It would've been very awkward if they'd gotten there, rip-raring to go, and not gotten a table.

He was beginning to like Dean.

He hadn't seen much out of Sam, not yet at least. But he had a feeling that he was going to see much more of Sam later.

They arrived at the Crossroads quick enough, and true to the holiday, it was packed full to bursting. The line stretched halfway around the block, for hell's sake.

As soon as they walked up, a hostess walked out in the traditional all-black uniform with a smile plastered on her overdone face, and began to lead the three to a booth in the back of the resturant. As they bypassed the line, they earned several nasty stares and even a couple of pointed comments.

"Let's just hope that that was about us skipping the line, not about us in general." Sam said, nudging Dean's shoulder.

The booth was fabulous. The seats were coated in a dark black leather, a red tablecloth covered the deep cherry-stained table beneath and on top of the table, the proverbial cherry on top of the ice cream, was a bouquet of roses.

He whistled. "Crowley must owe you a lot of favors."

Sam winked. "Damn right he does."

Crowley was the owner, founder, and manager of the Crossroads. He was, at best, a little prickly, at worst, he was downright rude as all hell. Whatever dirt Sam had on him, it was big.

"Caught him fucking one of my dad's old friends. Needless to say, he doesn't want it getting out." Sam said, almost on cue. "Probably set his dog after me for telling you."

Dean smiled. "He set that beast on me once. What was its name? Growley?"

He chuckled. "I've only heard about Growley. Looks to be a good thing, the way you are both talking about the poor mutt."

Sam laughed. "Best keep it that way, Cas. Believe me, word of mouth is the closest you want to get to it." Sam froze. "Is that… alright? Can I call you Cas?"

He nodded. "Cas is fine, just… unusual. Never heard it used about me before."

Dean smiled. "Well, it's stuck now. Castiel was a mouthful anyways."

He puffed up his chest, indignant. "Castiel is an angelic name, if you must know. Angel of Thursday. It's a great name."

Sam laughed. "Whatever you say, Cas."

And at that moment, the waitress from earlier decided to come around. From up close, you could tell that the smile she wore was just as fake as the dusky eyeshadow around her browbones. The nametag she wore pinned to her breast read _Bela. _

"Hey honeys, what can I get you to drink?" she asked chirpily. He was tempted to tell her that her smile wasn't fooling any of any of them, but he let it pass. Some things should be left unsaid.

"I'll have a house beer." Dean said, his eyes popping up from the other two to focus on their waitress.

Sam and Cas shared a look. "Make that three." Sam said.

Bela glared between them. "I better be seeing some I.D., young men."

They all scrambled to reach their wallets as Bela stared down at them. He got his out of his back jeans pocket with relatively little difficulty, Dean as well, but Sam was having a little trouble.

"Oh, shit." Sam said. "I forgot my wallet."

Dean sighed in exasperation. Apparently, this wasn't the first time.

Him and Dean showed Bela their drivers licenses, which both showed them as twenty-one. Bela huffed, and turned away, but not without a pointed glance that said _if you two share your beers with him, you will be leaving this establishment faster than you can say hellhound._

Sam slumped back into his booth section, a dejected look on his face. "Awww, don't worry, Sammy. Your I.D. proves that you're only twenty anyways."

Sam shot daggers at him. "This means that I can't get shitfaced drunk on New Years Eve, Dean. Not funny."

Cas spoke up, eager to be included in the conversation. "Well at least we'll have a designated driver."

All three cracked a smile at that. Of course, all of them had walked here, but one sober person wouldn't hurt.

And then, Bela came back, bearing two of the house draft and one tall glass of water for Sam. "I see any of you sharing…" she said, before staring daggers at Dean.

He crumpled underneath her gaze. "Promise on my parent's grave."

She sniffed. "Good. Now, what do you guys want to eat?"

They left the Crossroads full-stomached and ultimately satisfied.

Cas was beginning to get a tad woozy from the three beers he'd consumed at the Crossroads, and Dean wasn't doing much better.

"Hey, guys." Sam said. "Do you wanna go back to my dorm?"

They'd both nodded, still a little buzzed from the extra-potent House Ale.

Sam had gotten the Cobb salad at Crossroads, despite his and Dean's protests _that he had to eat some real food, that stuff was digusting _and all Sam had said was t_hat at least he was going to die of cholesterol poisoing a little later in life. _

Of course, he and Dean had ordered the Hellhound special: a double bacon cheeseburger, topped with fried onions, Thousand Island, and their 'special sauce' (which, at this point, Dean believed was just raw pepper juice and mayonnaise).

The streetlights glared down at them, shining in their eyes and making them blink with every glance upwards. Oh, well. Better seeing infra-black than getting mugged.

It didn't take them excessively long to make their way to Sam's dorm. The dorm was only two blocks away from where they'd met in the first place, so they only walked about four blocks.

The entire way there, they played Q and A: when Dean's birthday was (January 24th), what Sam's dog was called (Bones), and what his favorite color was (sunset orange). They'd played about seven rounds of the infernal game before they got to the door of Sam's apartment.

And suddenly he was kissing Dean, hard, and maybe it was the alcohol taking the edge off a little bit, or maybe it was the fact that it was New Years Eve and this kind of shit behavior was supposed to happen, but he wasn't going to be letting go anytime soon.

Dean melted into the kiss, the kisses, with pants and moans and even one pained shout of what sounded like part of a prayer.

And the entire time, Sam had the decency to stand there with a shocked expression on his face, honestly surprised at the ferocity behind the art student (they'd discussed majors back at the resturant; Sam was pre-law, and Dean was automotive mechanics).

He broke away from the kiss long enough to viciously nod at Sam to _yes, get the damn door open, we want to all have sex and that does include you too._

Sam's hands jiggled with the keys, trying to open the door as fast as possible because to hell he be damned if he was going to wait any longer to get in on that action.

When the door opened, it carried his and Dean's momentum with it, sending them stumbling into the scenic stage of Sam's dorm suite. It was meticulously clean, and quite colorful, but he wasn't exactly taking in the scenery.

No, what he was doing instead was grinding down on Dean, rubbing their cocks together as Sam shut the door behind them with the utmost speed and then Sam was there too, adding on to the friction fenzy that seemed to be building up in him as they worked.

Sam grabbed their collars, dragging them to a room in the back of the suite that he could only assume was Sam's. Sam threw the lock shut, and joined in again.

He and Sam grabbed Dean and threw him onto the bed, where Dean lay, fully dressed and panting. Sam and Castiel made quick work on the removal of Dean's clothing, only to stop and pull each other in for a filthy, sloppy kiss inbetween the act of popping the button on Dean's jeans.

Dean lay on the bed, full body exposed to the chill that ran through the dorms at all times (bastards too cheap to pay for fucking heating goddamn). As he watched Sam and Castiel kiss, his already rock-hard cock pulsed with blood. Damn if that didn't just turn him on.

Sam and him made quick work of their clothing, buttons popping and flying every which way. With all three fully in the nude, he made his way to the foot of the bed, while Sam made his way to the head.

Dean's head whipped around. "Wha—"

"Shhhhh." He whispered, trying to comfort Dean. "It'll feel good, don't you worry your pretty little head. Sam, do you have any lube?" he asked, slightly louder.

Sam nodded vigorously. "Yeah, there's some in the top drawer of the nightstand."

He scrambled off th bed to get the lube. As soon as he was back, with the springs of the cheap mattress creaking, he knelt inbetween Dean's legs. "Spread for me, sugar." He purred.

Dean whined, but did as he was told. As he inspected Dean, he smiled in satisfaction. "Never had anyone down there, huh? Pink little hole looks as fresh as the day that it came into this world."

Dean shook his head in confirmation. "Well, it'll feel good." He said. He popped the cap on the lube and began to coat his fingers in the smooth stuff. At the head of the bed, Sam was kissing him ferociously, taking away all of Dean's breath.

He looked up to the head of the bed, a smile playing upon his face, "Nuh uh, Sammy, you've gotta save some energy for me." He said. Sam relented, peppering Dean's face in softer, lighter kisses.

As he pressed a finger to Dean's taint, Dean gasped, and arched off the bed. "God – feels so good –"

"Oh, Dean, this is nothing. Just a warmup." He said.

His hand began to stroke Dean's cock, getting him nice and relaxed. That was the key.

Dean moaned laviciously, grappling at the sheets. _He was a puller. Nice._

He took his hand off of Dean's cock, relishing the little whine that escaped from the other mans throat. And then his finger was working, working at the ring of muscle surrounding Dean's hole, and Dean was letting off the most wonderful noises.

He was one finger in, up to the second knuckle now, and Dean was moaning and writhing in plesure below him, and Sam was still above him, covering him in kisses and words of encouragement. He added another finger, wrenching a loud moan from Dean's throat.

He was two fingers in, three knuckles deep, when he found it. He crooked his fingers, just the right way, and he had Dean arching off of the bed, shouting out his pleasure into the empty dorm suite.

Dean was in such a daze that he barely noticed when he added his third finger. With a glance between him and Sam, he knew that Sam, and Dean as well, were ready.

He pulled his fingers out of Dean's ass, enjoying the pained whine that emitted from the sandy haired man.

"Open up." Sam said, tapping Dean's chin lightly. And fuck, didn't that just turn him on.

He slid in, smooth and clean, relishing the sounds that Dean would've made, except for the face that Sam's cock was stuffed into his mouth, and he could deep throat like a pro _where did that come from - _

Dean snapped his hips up, in a very clear command. _Move. _

He began to move, slow thrusts at first, but faster as time went on. Dean was writhing beneath him, and Sam was right there, and –

Well, now he was kissing Sam, kissing him as they both thrust into different orifices of the man below him and he'll be damned if this wasn't the best way to lose your virginity.

Dean was moaning and twisting beneath them, completely and utterly overstimulated, begging for him to hit his sweet spot until he screamed.

What could he say, he could take orders sometimes.

He began to pump, harder, faster, until Dean was blacking out beneath him and he was seeing stars.

"Oh, fuck!" he yelled as he spent himself inside of Dean. Sam then came as well, flooding Dean's mouth with a wave of come that he managed to swallow the most of.

He and Sam pulled out of their respective bodily orifices, with no cringing or pulling away, period. Dean sighed beneath them, obviously content.

He checked the clock next to the bed and almost jumped out of shock. He hopped out of the bed and began to search for his jeans, pulling them on almost frantically. Both Dean and Sam looked up.

"What's the matter?" Dean asked, voice raw and rough from the face-fucking Sam had just given him. "Why are you getting dressed so quickly?"

"It's 11:57!" he hissed. "We need to go outside and watch the fireworks!"

Both Sam and Dean bolted upright, frantically searching the floor for the traces of their clothing. They eventually found them with out too much trouble, even if Sam's shirt was missing a few buttons and Dean's pants had a broken zipper.

11:59. 1 minute.

All three raced down the three flights of stairs, feet thumping roughly as they raced out to the front lawn. Word was that it was the best place to see the fireworks. They weren't gonna ignore the common word now, even if they did just about every other town.

10.

9.

8.

7.

6.

5.

4.

3.

2.

1.

The bells rung, the paper horns tooted, the vague sound of Auld Lang Syne drifted over the crowd. But no one was paying attention to that ghastly song. No, all their attention was on the colorful display of fireworks currently shooting up all over the sky.

He turned to Sam and Dean. "Kiss at midnight, right?"

And as they both turned in to kiss him, his only thought was that he might have to thank Gabriel later for this. For once, he hadn't fucked up.

And the sex was great.


End file.
